We are closing on our first contract the end of the month. Is it a good financial decision? Well probably not. From a financial perspective there are certainly other avenues to take with your money. But are the lifelong family memories worth it? For us, absolutely...I consider myself a pretty frugal person and think carefully before spending money on unnecessary things. But I’ve also learned that life experiences truly are priceless and being frugal is also what is allowing our family to afford this lifelong luxury. And last but not least, historically speaking, DVC has and might continue to go up in value so if you happen to have buyers remorse in a few years you’re not losing it all. Depending on many circumstances you could break even or maybe even come ahead.
So march forward with confidence and don’t look back!
The more I surf these boards, the more like-minded people I find! I am FRUGAL from birth; it's in my Scottish DNA

My grandparents, having lived through the Great Depression, would re-use tea-bags, squeeze a toothpaste tube inside out before discarding it with any toothpaste left inside, and pinched pennies until Lincoln had a migraine. My parents were not quite together on that philosophy however; my Mom was a Saver, but my Dad liked to spend what he had. He was a "live for today" person. I inherited a good bit from both, and have gotten to a philosophy similar to yours. I pinch-pennies, clip coupons, buy gift cards when they're on sale, especially when I use my Disney Visa to buy Disney Gift Cards when on sale at BJs!!, and will wear a pair of shoes until the soles are worn through, but when it's time for vacation, or to celebrate a family event, I spend like a drunken sailor.
(no offense to any DVCers who are in the Navy)

But, right after each "splurge", I can't help but start plotting how to save on something else, to offset some of the incurred expenses.
Our latest trend: We accumulate all our Chick-Fil-A points throughout the year, hold tight to restaurant gift cards that we get for Birthdays/Anniversaries/Christmas, save our Landry's points,(and we both have listed our Birthdays with Landrys in the months we typically travel to Disney), and cash in our Disney Visa CC Points for a Gift Card just prior to our trip, and then we see how long we can go at WDW without paying "out of pocket" for food! Simultaneously, we have no hesitation in making ADRs at our favorite Disney restaurants, but we also leave there with our "doggie-bags", and eat leftovers in our DVC rooms for a couple nights afterward...........
